7-(benzyloxy)-3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine → 3-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[D]azepin-7-OL

HRID 645805Notes

Reaction equation

HRID 645805 reaction equation
C([O:8][C:9]1[CH:23]=[CH:22][C:12]2[CH2:13][CH2:14][N:15]([CH:18]3[CH2:21][CH2:20][CH2:19]3)[CH2:16][CH2:17][C:11]=2[CH:10]=1)C1C=CC=CC=1>C(O)C.O1CCCC1.[Pd]>[CH:18]1([N:15]2[CH2:16][CH2:17][C:11]3[CH:10]=[C:9]([OH:8])[CH:23]=[CH:22][C:12]=3[CH2:13][CH2:14]2)[CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 1

HCID 102447167-(benzyloxy)-3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 100820813-Cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[D]azepin-7-OL

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-Benzyloxy-3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (E1) (9.22 g, 30 mmol) was dissolved in ethanol (150 ml) and tetrahydrofuran (50 ml). Palladium (1.5 g, 10% on charcoal paste) was added and the reaction mixture was stirred at room temperature under hydrogen (1 atmosphere) for 5 hours. The reaction mixture was filtered through celite and the filtrate concentrated in vacuo. The crude residue was triturated with diethyl ether and filtered to afford the title product (E3); MS (ES+) m/e 218 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe crude residue was triturated with diethyl ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-b19e574d3bbf4431bba4bada5f5e063b
Source dataset
uspto-grants-2010_04
Patent number
US07704994B2

Reaction notes

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